Potassium Carbonate → 1-(4-{4-[7-amino-2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}piperidin-1-yl)ethanone diformate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodo-2-(thieno[2,3-d]pyridazin-3-yl)furo[2,3-c]pyridin-7-amine (7.0 mg, 0.018 mmol), 1-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidin-1-yl}ethanone (6.80 mg, 0.0213 mmol), (1,1′-bis-(diphenylphosphino)-ferrocene) palladium dichloride (14.6 mg, 0.020 mmol), and potassium carbonate (6.14 mg, 0.0444 mmol) in 1,4-dioxane (0.5 mL) and water (0.2 mL) was irradiated under microwave heating at 120° C. for 60 min. The sample was passed through a syringe filter and purified by preparative HPLC to afford 5.2 mg (50%) of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 10.29 (s, 1H), 9.86 (s, 1H), 8.85 (s, 1H), 8.24 (br s, 2H), 8.19 (s, 1H), 7.95 (s, 1H), 7.90 (s, 1H), 7.71 (s, 1H), 4.70 (d, J=11.87 Hz, 1H), 4.55 (t, J=11.37 Hz, 1H), 4.12 (d, J=13.64 Hz, 1H), 3.33-3.41 (m, 1H), 3.21 (q, J=7.16 Hz, 1H), 2.88 (t, J=13.01 Hz, 1H), 2.18 (s, 3H), 2.12-2.30 (m, 3H); MS (ESI): 460.29 [M+H]+; HPLC tR=2.40 min.

Provenance & Evidence